It is funny how our kids can reawaken old interests for us. As I mentioned a few weeks ago, my eldest son started playing organized roller hockey this year. Aside from becoming a quite loud vocal presence at his games, I was also inspired to buy some gear and start practicing with him. I have already addressed the interplay between the Biglaw and boutique “lifestyle” regarding the latter. This week, I want to address another “side effect” of my rekindled interest in hockey. Because you are forced to confront where you stand when something happens in your current reality that sparks memories of an earlier time.

So after a long-hiatus, I have been watching a fair amount of playoff hockey lately. Especially Rangers games, like a good number of my fellow New Yorkers. And when the Rangers made the Stanley Cup by beating the Canadiens a few nights ago, my thought process went like this: “Wow, the Rangers made the Cup!” followed by “This is great, if they win it will be their first Cup since ‘94!” followed by “Hey, I remember senior year in high school when the Rangers winning the Cup was a huge deal” followed by “No way, I graduated high school TWENTY years ago!”

That feels like a very long time. But despite the passage of time, I can also remember certain things from back then as if they just happened….

For example, I have a very vivid memory of one day late in senior year. It was well past the date of AP and Regents exams, and the faculty had long despaired of trying to teach us anything during class time. My homeroom class in high school was a large one, with over thirty students. For the four years prior we had spent most of our waking hours together (I went to a dual-curriculum yeshiva high school, and we had scheduled classes from 8 to 5:30 most days), and everyone was now looking forward to college and beyond. So we were sitting around, talking about ourselves with the righteousness that only teenagers can muster, and predicting the careers that we thought everyone in the class would have. It was twenty years ago, but I can remember where I was sitting, and how everyone was arranged in the room. There was a purity to that discussion, and the history together that preceded it. So I remember.

Viewing that scene from the distance of a long-held memory, I can only imagine now what high-school-senior me would think about how my life and career has turned out so far. Other than Jacoby & Meyers, I would have been hard pressed to have named a single law firm back then. And I can’t recall having had any interaction at all with the “legal system” — at least before a traffic ticket I got while in college forced me to into a “plea deal” with a quite dispirited municipal prosecutor in a Jersey Shore “courtroom.”

So the idea that I would work as a patent lawyer, or ever make partner at a large international law firm, was never even a consideration for me at the time. Or that my practice would take me around the world, and allow me to interact with everyone from sole inventors to multinational corporations. Twenty years may not seem as too long ago, but it was long enough ago that none of us had cell phones, and if you wanted to talk, you needed to call on the “house phone.” It was a big deal for someone to “have their own line,” and no one I knew was using email or instant messaging. Other than the ubiquity of the Clintons in the prevailing political discourse of the day, it was a very different world than the one we have today.

The benefit I can see regarding thinking about a past version of yourself is not tied up, however, in a comparison of what you owned back then versus what you own now. Or even whether you ended up acquiring the things you used to want, or achieved the accomplishments that you had set out to achieve. Just as the benefit of thinking about your future is not necessarily about setting goals or trying to plan how your life will look twenty years from now. What really matters is whether you can “answer to yourself” with respect to the choices you made and the values you espoused. And what you are willing to do to get to where you feel you “need” or are “supposed” to be in the future.

So I would not really want to tell my high-school self what to expect. Or give him pointers about what courses to take in college, which law school to try and get into, or even which partners to avoid while a Biglaw associate. What I would remind him is that while circumstances, technology, and even the people in his life would change, his happiness would mostly be tied to how closely he hewed to the values that he held important. I would also encourage him to do as much as he could to help out others, because that is the responsibility of the fortunate to those less so. And I would definitely tell him to ignore the career prediction that his classmates made for him. Republican speechwriter? I’d rather have an ATL column.

Please feel free to send comments or questions to me at gkroub@kskiplaw.com or via Twitter: @gkroub. Any topic suggestions or thoughts are most welcome.

Gaston Kroub lives in Brooklyn and is a founding partner of Kroub, Silbersher & Kolmykov PLLC, an intellectual property litigation boutique. The firm’s practice focuses on intellectual property litigation and related counseling, with a strong focus on patent matters. You can reach him at gkroub@kskiplaw.com or follow him on Twitter: @gkroub.

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